Water → HCID 18326755, compound

HRID 1250465Notes

Reaction equation

HRID 1250465 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:22][CH2:23][CH:24]([OH:27])[CH2:25][OH:26].O.Cl.CCOCC>CO>[ClH:1].[CH2:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20][CH2:21][N:12]1[C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([NH:22][CH2:23][CH:24]([OH:27])[CH2:25][OH:26])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 735613-Amino-1,2-propanediolHCID 10953452Ether hydrochlorideHCID 11483278HCID 11483278, compound

Product 1

HCID 18326755HCID 18326755, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
155 °C

Procedure

2-Chloro-4-(3,4-dihydro-1H-isoquinolin-2-yl)-quinoline (0.44 g, 1.5 mmol) and (RS)-3-amino-1,2-propanediol (0.82 g, 9.0 mmol) were mixed and heated at 150-160° C. for 5 hours. The reaction mixture was cooled to room temperature and water (15 ml) was added. The resulting solid was filtered, dried and chromatographed over silica gel (CH2Cl2—MeOH, 19:1 then 9:1) to provide a white foam which was dissolved in MeOH. HCl—Et2O was added to provide (RS)-3-[4-(3,4-dihydro-1H-isoquinolin-2-yl)-quinolin-2-ylamino]-propane-1,2-diol hydrochloride (0.4 g, 69%) as an offwhite foam, MS: m/=349 (M+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting solid was filtered
  3. customdried
  4. customchromatographed over silica gel (CH2Cl2—MeOH, 19:1
  5. custom9:1) to provide a white foam which

Sources & evidence

ORD record
ord-82bdba47e2a24bfea52e269f035af4e5
Source dataset
uspto-grants-2002_01
Patent number
US06339093B1

Reaction notes

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